Synthesis of new codeinone and indolinocodeinone derivatives

Derivatives of both 14-hydroxycodeinone and the Diels-Alder adducts of thebaine provide some of the most potent analgesics in the morphine–thebaine group of alkaloids. As an extension to the range of available compounds the preparation of modified thebaines and 14-N-substituted codeinones was a desirable objective. The synthesis of 7-alkyl- or aryl thebaines from salutaridine via the corresponding salutaridinols was attempted but the acid-catalysed cyclisation of the latter was not successful. [Continues.]